Compounds > n-(3-oxo-octanoyl)-l-homoserine lactone
Page last updated: 2024-11-07

n-(3-oxo-octanoyl)-l-homoserine lactone

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Description

N-(beta-oxooctan-1-oyl)homoserine lactone: involved in conjugation and tra gene regulation in Agrobacterium tumefaciens; structure in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID127293
CHEMBL ID463321
SCHEMBL ID1080050
MeSH IDM0215124

Synonyms (40)

Synonym
n-(beta-ketooctanoyl)-l-hsl
n-(beta-oxooctan-1-oyl)-l-homoserine lactone
n-(beta-oxooctan-1-oyl)homoserine lactone
cf1, a. tumefaciens
aai-oohl
octanamide, 3-oxo-n-(tetrahydro-2-oxo-3-furanyl)-, (s)-
n-(3-oxo-octanoyl)-l-homoserine lactone
conjugation factor 1, agrobacterium
LMFA08030004
n-(3-oxo-octanoyl)-homoserine lactone
n-(3-oxooctanoyl)homoserine lactone
oohl
n-(3-oxooctanoyl)-l-homoserine lactone
147795-39-9
3-oxo-octanoic acid (2-oxo-tetrahydro-furan-3-yl)-amide
n-(3-oxo-octanal-1-yl)-homoserine lactone
n-(3-oxooctanoyl)-l-homoserine lactone, >=97% (hplc), white powder
3-oxo-c8-hsl
ai-1 (a. tumefaciens)
autoinducer 1 (a. tumefaciens)
aai-1
DB08081
CHEMBL463321 ,
3-oxo-n-[(3s)-2-oxooxolan-3-yl]octanamide
bdbm50351511
n-3-oxo-octanoyl-l-homoserine lactone
SCHEMBL1080050
3-oxo-n-[(3s)-tetrahydro-2-oxo-3-furanyl]octanamide
FXCMGCFNLNFLSH-JTQLQIEISA-N
octanamide, 3-oxo-n-[(3s)-tetrahydro-2-oxo-3-furanyl]-
mfcd08277025
DTXSID60163802
J-008413
3-oxo-n-[(3s)-2-oxotetrahydrofuran-3-yl]octanamide
Q27097310
n-beta-oxo-octanoyl-l-homoserine lactone
HY-108700
CS-0030129
PD004806
Z3301590447
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Protein Targets (2)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Transcriptional activator protein LasRPseudomonas aeruginosa PAO1IC50 (µMol)2.80500.11003.15839.0000AID1604885; AID615272
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Activation Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Transcriptional activator protein LasRPseudomonas aeruginosa PAO1EC50 (µMol)100.07500.00150.06570.1500AID1604886; AID615273
LuxR family transcriptional regulator Pseudomonas aeruginosaEC50 (µMol)0.01100.01100.01590.0220AID318815
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Bioassays (20)

Assay IDTitleYearJournalArticle
AID1604886Activation of LasR in Pseudomonas aeruginosa PAO-JP2 harboring plasI-LVAgfp incubated for 6 hrs by fluorescence method2020Bioorganic & medicinal chemistry, 02-01, Volume: 28, Issue:3
Impact of the structure-activity relationship of AHL analogues on quorum sensing in Gram-negative bacteria.
AID152943Inhibition of human peripheral blood mononuclear cell (PBMC)donor C proliferation2003Journal of medicinal chemistry, Jan-02, Volume: 46, Issue:1
Synthetic analogues of the bacterial signal (quorum sensing) molecule N-(3-oxododecanoyl)-L-homoserine lactone as immune modulators.
AID615222Antagonist activity at Agrobacterium tumefaciens TraR receptor in presence of 100 nM 3-oxo-C8-HSL2010Journal of medicinal chemistry, Nov-11, Volume: 53, Issue:21
Medicinal chemistry as a conduit for the modulation of quorum sensing.
AID395857Agonist activity at Escherichia coli DH5alpha LasR receptor by beta-galctosidase reporter gene assay2008Bioorganic & medicinal chemistry letters, Nov-15, Volume: 18, Issue:22
Evaluation of a focused library of N-aryl L-homoserine lactones reveals a new set of potent quorum sensing modulators.
AID152953Inhibition of LPS-induced human TNF-alpha secretion; ND means not determined.2003Journal of medicinal chemistry, Jan-02, Volume: 46, Issue:1
Synthetic analogues of the bacterial signal (quorum sensing) molecule N-(3-oxododecanoyl)-L-homoserine lactone as immune modulators.
AID615272Antagonist activity at Pseudomonas aeruginosa LasR receptor expressed in Escherichia coli in presence of 7.5 nM natural auto-inducer 3-oxo-C12-HSL2010Journal of medicinal chemistry, Nov-11, Volume: 53, Issue:21
Medicinal chemistry as a conduit for the modulation of quorum sensing.
AID1604888Activation of LasR in Escherichia coli JLD271 harboring pSC11/pJN105L using CPRG as substrate incubated for 4 hrs by Miller assay method2020Bioorganic & medicinal chemistry, 02-01, Volume: 28, Issue:3
Impact of the structure-activity relationship of AHL analogues on quorum sensing in Gram-negative bacteria.
AID1604885Inhibition of LasR in Pseudomonas aeruginosa PAO-JP2 harboring plasI-LVAgfp incubated for 6 hrs by fluorescence method2020Bioorganic & medicinal chemistry, 02-01, Volume: 28, Issue:3
Impact of the structure-activity relationship of AHL analogues on quorum sensing in Gram-negative bacteria.
AID318820Inhibition of Pseudomonas aeruginosa LasR2008Bioorganic & medicinal chemistry letters, May-15, Volume: 18, Issue:10
Synthetic ligands that activate and inhibit a quorum-sensing regulator in Pseudomonas aeruginosa.
AID395858Agonist activity at Vibrio fischeri ES114 LuxR receptor by luciferase reporter gene assay2008Bioorganic & medicinal chemistry letters, Nov-15, Volume: 18, Issue:22
Evaluation of a focused library of N-aryl L-homoserine lactones reveals a new set of potent quorum sensing modulators.
AID142576Inhibition of murine splenocyte proliferation2003Journal of medicinal chemistry, Jan-02, Volume: 46, Issue:1
Synthetic analogues of the bacterial signal (quorum sensing) molecule N-(3-oxododecanoyl)-L-homoserine lactone as immune modulators.
AID152941Inhibition of human peripheral blood mononuclear cell (PBMC)donor A proliferation2003Journal of medicinal chemistry, Jan-02, Volume: 46, Issue:1
Synthetic analogues of the bacterial signal (quorum sensing) molecule N-(3-oxododecanoyl)-L-homoserine lactone as immune modulators.
AID318815Agonist activity at Pseudomonas aeruginosa QscR expressed in Escherichia coli assessed as production of beta-galactosidase2008Bioorganic & medicinal chemistry letters, May-15, Volume: 18, Issue:10
Synthetic ligands that activate and inhibit a quorum-sensing regulator in Pseudomonas aeruginosa.
AID615273Agonist activity at Pseudomonas aeruginosa LasR cognate receptor expressed in Escherichia coli harboring pKDT17 assessed as activation of lasB expression by LacZ reporter gene assay2010Journal of medicinal chemistry, Nov-11, Volume: 53, Issue:21
Medicinal chemistry as a conduit for the modulation of quorum sensing.
AID615275Induction of quorum sensing regulated bioluminescence in Vibrio fischeri by luminescence assay relative to natural autoinducer2010Journal of medicinal chemistry, Nov-11, Volume: 53, Issue:21
Medicinal chemistry as a conduit for the modulation of quorum sensing.
AID152955Inhibition of human peripheral blood mononuclear cell (PBMC)donor B proliferation; ND means not determined.2003Journal of medicinal chemistry, Jan-02, Volume: 46, Issue:1
Synthetic analogues of the bacterial signal (quorum sensing) molecule N-(3-oxododecanoyl)-L-homoserine lactone as immune modulators.
AID615221Antagonist activity at Vibrio fischeri luxR receptor in presence of 5 uM 3-oxo-C6-HSL2010Journal of medicinal chemistry, Nov-11, Volume: 53, Issue:21
Medicinal chemistry as a conduit for the modulation of quorum sensing.
AID318814Agonist activity at Pseudomonas aeruginosa QscR expressed in Escherichia coli assessed as production of beta-galactosidase at 5 uM relative to dodecanoyl homoserine lactone2008Bioorganic & medicinal chemistry letters, May-15, Volume: 18, Issue:10
Synthetic ligands that activate and inhibit a quorum-sensing regulator in Pseudomonas aeruginosa.
AID395856Agonist activity at Agrobacterium tumefaciens WCF47 TraR receptor by beta-galctosidase reporter gene assay2008Bioorganic & medicinal chemistry letters, Nov-15, Volume: 18, Issue:22
Evaluation of a focused library of N-aryl L-homoserine lactones reveals a new set of potent quorum sensing modulators.
AID1604887Inhibition of LasR in Escherichia coli JLD271 harboring pSC11/pJN105L using CPRG as substrate incubated for 4 hrs by Miller assay method2020Bioorganic & medicinal chemistry, 02-01, Volume: 28, Issue:3
Impact of the structure-activity relationship of AHL analogues on quorum sensing in Gram-negative bacteria.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (33)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's7 (21.21)18.2507
2000's15 (45.45)29.6817
2010's10 (30.30)24.3611
2020's1 (3.03)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 11.00

According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be weak demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index11.00 (24.57)
Research Supply Index3.53 (2.92)
Research Growth Index4.53 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (11.00)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews1 (3.03%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other32 (96.97%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]
SubstanceRelationship StrengthStudiesTrialsClassesRoles
gamma-aminobutyric acid
gamma-Aminobutyric Acid: The most common inhibitory neurotransmitter in the central nervous system.. gamma-aminobutyric acid : A gamma-amino acid that is butanoic acid with the amino substituent located at C-4.		2.4420amino acid zwitterion;
gamma-amino acid;
monocarboxylic acid		human metabolite;
neurotransmitter;
Saccharomyces cerevisiae metabolite;
signalling molecule
catechol
[no description available]		2.0510catecholsallelochemical;
genotoxin;
plant metabolite
pyrogallol
benzenetriol : A triol in which three hydroxy groups are substituted onto a benzene ring.		2.0510benzenetriol;
phenolic donor		plant metabolite
mannitol
[no description available]		210mannitolallergen;
antiglaucoma drug;
compatible osmolytes;
Escherichia coli metabolite;
food anticaking agent;
food bulking agent;
food humectant;
food stabiliser;
food thickening agent;
hapten;
metabolite;
osmotic diuretic;
sweetening agent
arginine
Arginine: An essential amino acid that is physiologically active in the L-form.. arginine : An alpha-amino acid that is glycine in which the alpha-is substituted by a 3-guanidinopropyl group.		210arginine;
glutamine family amino acid;
L-alpha-amino acid;
proteinogenic amino acid		biomarker;
Escherichia coli metabolite;
micronutrient;
mouse metabolite;
nutraceutical
4-butyrolactone
4-Butyrolactone: One of the FURANS with a carbonyl thereby forming a cyclic lactone. It is an endogenous compound made from gamma-aminobutyrate and is the precursor of gamma-hydroxybutyrate. It is also used as a pharmacological agent and solvent.. tetrahydrofuranone : Any oxolane having an oxo- substituent at any position on the tetrahydrofuran ring.. gamma-butyrolactone : A butan-4-olide that is tetrahydrofuran substituted by an oxo group at position 2.		3.93120butan-4-olidemetabolite;
neurotoxin
pyrroles
1H-pyrrole : A tautomer of pyrrole that has the double bonds at positions 2 and 4.. pyrrole : A five-membered monocyclic heteroarene comprising one NH and four CH units which forms the parent compound of the pyrrole group of compounds. Its five-membered ring structure has three tautomers. A 'closed class'.. azole : Any monocyclic heteroarene consisting of a five-membered ring containing nitrogen. Azoles can also contain one or more other non-carbon atoms, such as nitrogen, sulfur or oxygen.		2.0710pyrrole;
secondary amine
homoserine
homoserine : An alpha-amino acid that is glycine substituted at the alpha-position by a 2-hydroxyethyl group.. L-homoserine : The L-enantiomer of homoserine.		4.26180amino acid zwitterion;
homoserine		algal metabolite;
Escherichia coli metabolite;
human metabolite;
Saccharomyces cerevisiae metabolite
acetosyringone
acetosyringone: plant inducer which induces expression of VirE & VirG in A. tumefaciens. acetosyringone : A member of the class of acetophenones that is 1-phenylethanone substituted by a hydroxy group at position 4 and methoxy groups at positions 3 and 5.		2.0310acetophenones;
dimethoxybenzene;
phenols		anti-asthmatic drug;
non-narcotic analgesic;
non-steroidal anti-inflammatory drug;
peripheral nervous system drug;
plant metabolite
2,3,4-trihydroxbenzophenone
2,3,4-trihydroxbenzophenone : A benzenetriol that is benzophenone in which one of the phenyl groups is substituted by hydroxy groups at positions 2, 3, and 4. It is a redox mediator.		2.0510benzenetriol;
hydroxybenzophenone		drug metabolite;
EC 1.14.18.1 (tyrosinase) inhibitor;
human urinary metabolite;
quorum sensing inhibitor;
rat metabolite
nopaline
nopaline: utilized by virulent strains of Agrobacterium; metabolites of crown-gall tumors; isonopaline refers to (R-isomer) of nopaline; structure. D-nopaline : An amino acid opine resulting from the formal reductive condensation of the amino group of L-arginine with the keto group of 2-oxopentanedioic acid.		210amino acid opine;
D-glutamic acid derivative;
guanidines;
L-arginine derivative;
secondary amino compound;
tricarboxylic acid
n-(3-oxohexanoyl)-3-aminodihydro-2(3h)-furanone
N-(3-oxohexanoyl)-3-aminodihydro-2(3H)-furanone: cpd synthesized by luminous bacteria excreted into medium that induces luciferase synthesis at threshold concentration; structure in first source. N-(3-oxohexanoyl)homoserine lactone : A N-acyl homoserine lactone that is the monocarboxylic acid amide resulting from the formal condensation of the carboxy group of 3-oxohexanoic acid with the amino group of homoserine lactone.		2.4220N-acyl homoserine lactone;
secondary carboxamide
mannopine
mannopine: mannityl opine analog; RN given refers to (S)-isomer. mannopine : A hexitol derivative that is D-mannitol in which the hydroxy group at position 1 is replaced by the alpha-amino group of L-glutamine. It is produced in crown gall tumours induced in a wide range of dicotyledenous plants by Agrobacterium tumefaciens.		210amino acid opine;
dicarboxylic acid monoamide;
hexitol derivative;
L-glutamine derivative;
non-proteinogenic L-alpha-amino acid;
secondary amino compound		plant metabolite
agrocinopine
agrocinopine: opine phosphorylated sugar synthesized by crown gall tumors & utilized as nutrient source by bacteria responsible for infection. agrocinopine : A subclass of opines, which are low molecular weight compounds found in plant crown gall tumours or hairy root tumours produced by parasitic bacteria of the genus Agrobacterium. Agrocinopines are set of sugar phosphodiester opines known to induce transfer of another Ti plasmid, pTiBo542.. agrocinopine A : A member of the class of agrocinopines that consists of sucrose and L-arabinose units joined via a phosphodiester linkage between position 4(F) of sucrose and position 2 of arabinose.		2.0510
n-heptanoyl-homoserine lactone
N-heptanoyl-homoserine lactone: structure in first source		3.6120N-acyl-amino acid
malonyl coenzyme a
Malonyl Coenzyme A: A coenzyme A derivative which plays a key role in the fatty acid synthesis in the cytoplasmic and microsomal systems.. omega-carboxyacyl-CoA : An acyl-CoA that results from the formal condensation of the thiol group of coenzyme A with one of the carboxy groups of any alpha,omega-dicarboxylic acid.		1.9910malonyl-CoAsEC 2.3.1.21 (carnitine O-palmitoyltransferase) inhibitor;
Escherichia coli metabolite;
metabolite;
mouse metabolite
nadp
[no description available]		1.9910
n-(3-oxododecanoyl)homoserine lactone
N-(3-oxododecanoyl)-L-homoserine lactone : An N-acyl-L-homoserine lactone having 3-oxododecanoyl as the acyl substituent.		4.2550N-(3-oxododecanoyl)homoserine lactone;
N-acyl-L-homoserine lactone		bacterial metabolite
homoserine lactone
homoserine lactone: a putative signal for starvation in E. coli; structure in first source. homoserinium lactone : The conjugate acid of homoserine lactone; major species at pH 7.3.. homoserine lactone : A butan-4-olide having an amino substituent at the 2-position.		2.1310ammonium ion derivative;
organic cation
daphnetin
[no description available]		2.0510hydroxycoumarin
cerulenin
Cerulenin: An epoxydodecadienamide isolated from several species, including ACREMONIUM, Acrocylindrum, and Helicoceras. It inhibits the biosynthesis of several lipids by interfering with enzyme function.. cerulenin : An epoxydodecadienamide isolated from several species, including Acremonium, Acrocylindrum and Helicoceras. It inhibits the biosynthesis of several lipids by interfering with enzyme function.		1.9910epoxide;
monocarboxylic acid amide		antifungal agent;
antiinfective agent;
antilipemic drug;
antimetabolite;
antimicrobial agent;
fatty acid synthesis inhibitor
selenium
Selenium: An element with the atomic symbol Se, atomic number 34, and atomic weight 78.97. It is an essential micronutrient for mammals and other animals but is toxic in large amounts. Selenium protects intracellular structures against oxidative damage. It is an essential component of GLUTATHIONE PEROXIDASE.		2.0110chalcogen;
nonmetal atom		micronutrient
n-hexanoyl-l-homoserine lactone
N-hexanoyl-L-homoserine lactone: structure in first source		2.0710N-acyl-amino acid
(S)-4,5-dihydroxypentane-2,3-dione
(S)-4,5-dihydroxypentane-2,3-dione : Pentane substituted at the 2- and 3-positions by oxo groups, at the 4- and 5-positions by hydroxy groups and with S stereoconfiguration at C-4.		2.0510alpha-diketone;
secondary alpha-hydroxy ketone		Escherichia coli metabolite
s-adenosylmethionine
(R)-S-adenosyl-L-methionine : An S-adenosyl-L-methionine that has R-configuration.. S-adenosyl-L-methionine zwitterion : A zwitterionic tautomer of S-adenosyl-L-methionine arising from shift of the proton from the carboxy group to the amino group.. (R)-S-adenosyl-L-methionine zwitterion : An S-adenosyl-L-methionine zwitterion that has R-configuration; major species at pH 7.3.. (S)-S-adenosyl-L-methionine zwitterion : An S-adenosyl-L-methionine zwitterion that has S-configuration; major species at pH 7.3.. S-adenosyl-L-methionine : A sulfonium compound that is the S-adenosyl derivative of L-methionine. It is an intermediate in the metabolic pathway of methionine.		1.9910organic cation;
sulfonium compound		coenzyme;
cofactor;
human metabolite;
micronutrient;
Mycoplasma genitalium metabolite;
nutraceutical;
Saccharomyces cerevisiae metabolite
clay
Clay: A naturally-occurring rock or soil constituent characterized by particles with a diameter of less than 0.005 mm. It is composed primarily of hydrous aluminum silicates, trace amounts of metal OXIDES, and organic matter.		2.1710
ConditionIndicatedRelationship StrengthStudiesTrials